Organic selenium compound for preventing and treating cancer
A compound and composition technology, applied in the field of selenium-containing organic compounds, can solve problems such as side effects, anti-cancer efficacy to be further improved, and limited structure types of compounds
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0086] Example 1: phenylselenoate 2-acetoxybenzoate
[0087] The reaction formula is as follows:
[0088]
[0089] Add phenylselenium chloride (1.51 g, 6.67 mmol) and 20 ml of anhydrous dichloromethane into a 50 ml flask, cool to -15°C in an ice-salt bath and stir, then add tributylphosphine (1.12 g, 5.56 mmol), 2-acetyl Oxybenzoic acid (1.00 g, 5.56 mmol) was protected by high-purity argon, kept at -15°C and stirred for 2.0 hours, and the reaction was complete as monitored by TLC. The solvent was distilled off under reduced pressure, separated by silica gel column chromatography, and ethyl acetate (V): Petroleum ether (V)=1:20 was used as the mobile phase to obtain 1.1 g of white needle-like crystals with a yield of 61%.
[0090] nuclear magnetic resonance 1 H NMR (400MHz, CDCl 3 ): 2.33 (s, 3H, CH 3 ), 7.16 (d, J = 8.00 Hz,1H, ArH), 7.35-7.43 (m, 4H, ArH), 7.56-7.59 (m, 3H, ArH), 7.97 (d, J = 8.00Hz, 1H, ArH ). 13 C NMR (100Hz, CDCl 3 ): 21.4, 124.3, 126.5, 129.3, ...
Embodiment 2
[0092] Example 2: 2-(4-isobutylphenyl)-phenylselenopropionate
[0093] The reaction formula is as follows:
[0094]
[0095] Add phenylselenide chloride (0.77g, 4.04 mmol) and 30ml of anhydrous dichloromethane into a 50ml flask, cool to -15°C in an ice-salt bath and stir, then add tributylphosphine (0.82g, 4.04 mmol), 2-( 4-Isobutylphenyl)-propionic acid (0.50g, 2.69mmol), passed through high-purity argon protection, kept stirring at -15°C for 2.0 hours, TLC monitored that the reaction was complete, distilled off the solvent under reduced pressure, and the silica gel column layer Analysis and separation, using ethyl acetate (V): petroleum ether (V) = 1:20 as the mobile phase, to obtain 0.72 g of colorless oily liquid II, with a yield of 74%.
[0096] nuclear magnetic resonance 1 H NMR (400MHz, CDCl 3 ): 0.90 (s, 3H, CH 3 ), 0.92 (s, 3H, CH 3 ), 1.55(d, J = 8.00 Hz, 3H, CH 3 ), 1.85 (m, 1H, CH), 2.48 (d, 2H, CH 2 ), 3.96 (q, J =8.00 Hz, 1H, CH), 7.14(d, J = 8.00 Hz, 2...
Embodiment 3
[0098] Example 3: (+)-α-Methyl-6-methoxy-2-naphthalene phenylselenoacetate
[0099] The reaction formula is as follows:
[0100]
[0101] Add phenylselenium bromide (0.77 g, 3.26 mmol) and 20 ml of anhydrous tetrahydrofuran into a 50 ml flask, cool to -15°C in an ice-salt bath and stir, then add tributylphosphine (0.88 g, 4.34 mmol), (+)-α -Methyl-6-methoxy-2-naphthaleneacetic acid (0.50g, 2.17 mmol), passed through high-purity argon protection, kept stirring at -15°C for 3.0 hours, TLC monitored the reaction was complete, and distilled off the solvent under reduced pressure, Separation by silica gel column chromatography, using ethyl acetate (V):petroleum ether (V)=1:8 as the mobile phase, afforded 0.66 g of white solid III with a yield of 83%.
[0102] nuclear magnetic resonance 1 H NMR (400MHz, CDCl 3 ): 1.63 (d, J = 8.00 Hz, 3H, CH 3 ), 3.92 (s,3H,CH 3 ), 4.12 (q, J = 8.00 Hz, 1H, CH), 7.14-7.18 (m, 2H, ArH), 7.30-7.34 (m,3H, ArH), 7.39-7.43 (m, 3H, ArH), 7.73 -7....
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More